


His Romping Pleasure

by kestra_troi



Category: Supernatural
Genre: Alley Sex, Anal Sex, Banter, Barebacking, Bottom Sam, Bottom Sam Winchester, Brother/Brother Incest, Clothed Sex, Come Shot, Deepthroating, Established Dean Winchester/Sam Winchester, Established Relationship, Hair Kink, Hair-pulling, Incest, M/M, Masturbation, No Plot/Plotless, Not Canon Compliant, Oral Sex, Plot What Plot/Porn Without Plot, Semi-Public Sex, Shameless Smut, Sibling Incest, Suit Sex, Top Dean, Top Dean Winchester, Top Dean Winchester/Bottom Sam Winchester, unprotected sex
Language: English
Status: Completed
Published: 2018-06-22
Updated: 2018-06-22
Packaged: 2019-05-27 02:34:18
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,575
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15014768
Author URL: https://archiveofourown.org/users/kestra_troi/pseuds/kestra_troi
Summary: Sam and Dean are on a case, but decide to have sex (in an alley) before doing their usual interviews.SMUT, obviously.No redeeming value, just another stop on the Wincestuous tour of America.Originally, this was part of a case fic, but I never actually got around to writing the case, so instead of leaving this shelved on my desktop, I decided to go ahead and post it. So here, you go: some random Wincest smut for you. Enjoy!





	His Romping Pleasure

**Author's Note:**

> Title is a small piece of a Michael Levenson quote about E.M. Forster, a queer, British author.
> 
> Kudos and comments welcome!

Parking the Impala in the first empty slot that they came across, Dean killed the engine and looked at his brother. “So, you wanna…?” Dean hiked his eyebrows up twice in quick succession, clearly with only one thing on his mind.

“Seriously?” Sam’s eyebrows furrowed, as he met Dean’s gaze.

“Why not?” Dean shrugged, pursing his lips. He briefly glanced around the neighborhood and found no red flags, nothing of significance that might deter his plan. He whipped his head back to Sam, the ‘we are a go’ signal beaming clearly from his facial expression and rolled his bottom lip between his teeth. Sam tracked the move and licked his lips.

Swiftly, so he wouldn’t be caught staring, he looked out the windshield, taking in their unimpressive surroundings. “Really? Here? Now?”       

“Sure! You, me, the alley. Just like always,” Dean confidently asserted. He slowly gazed down Sam’s body, like he could see beneath the FBI suit Sam wore. “You still, uh—”

“Yeah, Dean,” Sam hastily interjected, his cheeks lightly flushing as he hurriedly looked away to stare down at the Impala’s floorboard. His hole clenched, itchy at the mention of their romp back at their motel this morning. He squirmed in his seat. Still damp.

He turned his head to peer out his window, licking his lips and examining the sidewalk beside him and the alley directly across from them. Both were surprisingly empty given the time of day, and grimy the way streets tucked away from the tourist scene always are in big cities. But they had fucked in dirtier, seedier places than this.

They had a motel or an alley in every town they’d hit. Just another one of their traditions that didn’t get discussed but was followed religiously regardless. By comparison this alley didn’t seem so bad: a couple dumpsters, one-way only, surrounded on three sides by generically industrial buildings. 

“Yeah,” Sam muttered to himself. He undid his seatbelt. “Yeah, okay,” He added a little louder.

“Alright, Sammy!” Dean crowed, excitedly smacking Sam on the chest with his palm. He undid his seatbelt too. Sam opened his door and stepped out, absently fiddling with his suit jacket and surreptitiously scanning the street for possible trouble.

Trailing behind, Dean speed-walked to the sidewalk, buttoning his suit jacket and holding himself tightly upright as if strolling down this alley was part of some official business. Pretend and the world pretends with you. He caught up with Sam standing on the far side of the first dumpster that stood against the wall on the left against a brick warehouse.

“This one? Or the that one?” Dean tossed his chin in the direction of the second dumpster also along the same side but further down.

Sam sniffed, his hands on his hips, and studied the dumpster, the alley, and the street from this new perspective. He shrugged. “Dealer’s choice.”

“Let’s go one over. Looks fuller.” Nearly side by side they walked down the alley, Dean on the left and slightly behind Sam on the right. Once he reached the other side of the dumpster, Sam angled his body, so he could look down the alley one more time from this vantage point with his back to the far wall. Dean slid in past him, seeking the cover of the dumpster, and waited for the all-clear.

Assured that they were alone and not in any immediate danger of being discovered, Sam pressed his hand into Dean’s chest and gently pushed his older brother into the corner made by the dumpster and the wall. Dean went easy. Sam followed.

Dean undid his suit jacket buttons and moved to undo his belt, but Sam stopped him. “Clothes stay on,” he said, authoritatively. Dean startled, his mouth hanging open ready to protest. Sam stepped in again. “It’s the middle of the afternoon.”

“Alright, fine.” Dean groused, some of the wind going out of his sails. He held his hands up in surrender, mildly disgruntled. “But getting naked is half the fun.”

Incredulous, Sam chuckled, reaching low to squeeze his brother’s bulge. “Well, I guess the gay sex, in public, with me will have to be _all_ the fun, then.”

“Guess so,” Dean huffed, his dick throbbing in his pants, despite his disappointed tone. Sam rolled his eyes and smirked, staring Dean down as he slowly unzipped his brother’s slacks.

“So, what’re you saying? That the sex with me isn’t good?”

Dean met his gaze, unimpressed and refusing to take the bait. “Knock it off, dumbass.”

Slipping his hand into his brother’s pants, Sam hauled the rigid cock out into the open, the balls too, unencumbered as they were. They both ditched underwear right about the same time they had ditched any last lingering moral objections to brother-on-brother sex. It tended to just get in the way. All of it. And eventually, they just dropped it. Wholesale. No regrets.

Sam lightly stroked his brother’s shaft, teasingly thumbing the slit the way Dean liked.

“Sammy…” The back of Dean’s head plonked on the abrasive brick wall behind him as his hips jutted out, bucking into his brother’s featherlight touch. His eyes fluttered shut, his cheeks turned splotchy pink, and his dick rapidly hardened in the breezy, noxious air.

Squatting, Sam got eye level with Dean’s dick, twisting the shaft like he was churning a pepper grinder. “You bring any lube?”

“Glove compartment.” Dean rolled his hips into his brother’s tightened fist.

Glancing over his left shoulder, Sam briefly considered walking back to the Impala to grab the lube. He pursed his lips and frowned. “Forget it,” he mumbled, immediately lapping at the head of his brother’s dick like a popsicle before taking it into his mouth.

Dean slumped against the wall, murmuring his brother’s name as Sam insistently suckled the dripping tip and jerked the length he hadn’t wrapped his lips around yet.

“Condom’s back there too,” Dean breathily confessed, with no hint of shame. He opened his eyes and looked down waiting for the nagging to start. The younger, taller Winchester flicked his eyes up to meet his brother’s. He didn’t say a word or stop sucking dick for a single second, but his expression made it plain that he didn’t find Dean’s deliberate forgetfulness amusing.

Not admitting fault, Dean smiled. “I guess wet and messy will have to do, huh, Sammy?”

Sam grunted, disapprovingly. Testily, he swooped in low and swallowed the entire length in a single gulp. Dean swore, his hands shooting out, his fingers twining in Sam’s long locks on both sides of his head. He held his brother in place, minutely, leisurely thrusting his dick into Sam’s skilled throat.

“Sammy,” he groaned. He bit his bottom lip to keep from getting too loud. His devious brother flicked his tongue against his nuts and Dean shuddered all over, his grip instantly relaxing.

After a few more seconds of unaided deepthroating, Sam slurped his way off Dean’s dick and stroked the base with one hand while he wiped his chin off with the other, breaking the spit trails that fleetingly connected them. He spread the excess saliva over the thick head of his brother’s dick and hawked more, judiciously smearing his spit over Dean’s erection with both hands.

He let Dean guide his mouth back into range and opened wide as Dean pushed inside. His hands fell to his sides as his brother slowly but surely fucked his face. Spit dribbled down his chin and pooled in Dean’s man-scaped pubes. Quick and dirty and wet, just as they preferred.

Eventually, Dean let up. Sam sneaked a breath, quietly sniffling. He smacked his brother’s hands out of his hair. “Good enough,” he hoarsely intoned.                 

“That attitude, right there, is the reason you’re not a better lay.”

Sam snorted and got to his feet. “Yeah, well, we don’t have all day,” he said, making short work of his belt buckle. “They’re expecting us in about an hour.”

“Yeah, yeah,” Dean grumbled, rolling his eyes dismissively, unhappy that logic and reason once again wrecked his fun. He watched intently as Sam unbuttoned and unzipped his slacks. “Thought you said clothes stay on?”

“I’m not letting you rip another pair of my slacks,” Sam firmly asserted. He shoved his pants down over the swell of his ass but no farther and awkwardly shuffled closer to his brother. “Besides, it’s bad enough I’m letting you go raw right before we question—”

“Alright, alright, alright,” Dean griped. “Enough bitching. Just come ‘ere.”

“Now, who’s got the bad attitude?” Sam quipped.

“Hilarious, Sammy. Freakin’ hilarious,” Dean glared. Sam flashed a grin and spun on his heels. Now, facing away from his brother, he bent over, sticking his ass out as best he could given the constraints of his slacks.

Roughly stroking his dick, Dean slapped the leaking head solidly on Sam’s pert cheeks in annoyance and rucked up his suit jacket to keep it out of the way. Sam snickered and then gasped as Dean pressed the tip inside him without warning.

“Jerk,” he hissed under his breath.

“Bitch.” Dean swatted Sam’s ass a tad too harshly. Sam yelped breathily, and Dean did it again. “That’s what you get for being a Speedy Gonzalez.”

Bracing himself with one hand on the pockmarked brick wall and the other on his knee Sam pressed backwards into his brother’s lap. The burn rushed through him, painting his cheeks and his neck down to his collar bright red. He paused, to breath.

Gradually stepping forward, one foot at a time, Dean walked his dick into his brother with practiced ease until his whole length disappeared inside him. He grabbed Sam’s hips and yanked him the rest of the way until ass met hips. Sam noisily gulped slouching deeper into a better position.

“Hurry it up, Dean.” Sam checked his watch and raised his arm over his head for his brother to see. “Not much time.”

“You can’t rush perfection, Sammy,” Dean retorted. He reached forward with one hand and tightly seized a handful of his brother’s silky hair jerking his head back. Sam cursed. Dean pumped his hips once, short and forceful. “They’ll wait for us.”

“Dean…” Sam quivered, the rest of his squabbles vanishing as Dean began to fuck him in earnest, leaving behind only the stretch and the burn and the pleasure.

“This is how you fuck, Sammy,” Dean boasted between clenched teeth. He wrapped Sam’s hair tighter around his fingers and tugged. Sam moaned. His long, limp dick twitched. Dean pounded him harder, thrusting faster.

“God, Dean,” Sam whined, panting for air. His brother kept fucking it out of him. He arched his back for more and Dean gave it to him twice over.

“Yeah, that’s right, Sammy,” Dean gloated. “That’s right. FUCK.”

“Dean!” Sam took his hand away from the wall. The brothers shifted in unison while Sam started beating off under his brother; one hand on his dick, the other holding his tie out of the way against his chest. His dick grew hard in his hands in seconds as Dean rammed that place inside him with experienced, unsparing precision.

The frenzy hit.

In no time, Sam trembled, sweat dabbling his temples and come blasting out of him onto the dirty concrete at his feet. Some splattered unnoticed onto his dress shoes. His hole clenched.

Dean grunted, he growled, snapping his hips vehemently, nearly knocking Sam onto the ground with the force of his hips as he shot his load deep inside his younger brother. He leaned down low and stood on his tiptoes to brush his nose and his red-hot cheeks into the smooth, dark brown curls in his fist that smelled of that girly L’Oreal crap Sam loved to waste money on.

“Sammy…” Dean shivered, his balls pulling up for one last spurt. The moment passed, he dropped flat to his feet and released his hold on his brother’s hair.

Quick as a flash, Sam dropped to his knees and spun on his heels to suck the flecks of come and lube and ass off Dean’s dick. Dean moaned, squirming restlessly as he softened in Sam’s thorough, relentless mouth.

“Jesus, Sammy, come on,” Dean huffed, tumbling into the dumpster in his rush to get his dick some peace. He gently tucked his junk back into his slacks and zipped up. “Knock it off. Give a guy a rest. Geez.”

Standing to his full height, Sam halfheartedly glowered at his brother while he pulled up his pants and redid them. “You’re one to talk, Dean,” he snobbishly pointed out. “Twice in one day.”

“Yeah, yeah, whatever, Sammy. That’s different.” Dean waved his hand dismissively. He adjusted his clothes and rolled his shoulders. Without another word, he turned to his right and headed back to the Impala.

A short time later Sam followed, fully redressed, walking with a subtle limp. Dean paused at the mouth of the alley and quietly watched his brother, smirking when he noticed the limping. “Gotta little hitch in your giddy-up, there, Sammy?”

“Shut up, Dean,” Sam eloquently rebutted. They strolled to the car together, Dean practically gliding to the driver’s side like he was on cloud nine.

Sam placed his hand on the roof of the Impala waiting for his brother to unlock the car. He cleared his throat already kicking himself before he even said a word, but he couldn’t let this go. “But even you have to admit that this stuff, the stuff we do in these alleys is pretty, you know, gay.”

The door locks popped. Dean opened his door. “Whatever, dude. I’m straight.” Without nothing else to say, and so tired of having this particular conversation, Dean plopped into the driver’s seat and turned on his Baby.

Still standing on the curb, Sam scoffed and shook his head. The sheer amount of stubbornness... He opened his door and crouched low to take his seat. At the nadir of his curve, he farted, wetly.

“Dude, did you just—”

“Shut up, Dean,” Sam barked, his face reddening. He slammed his door closed and fussed with his seatbelt, steam billowing from his ears as Dean had himself a nice laugh at his expense. The dirty look he gave Dean could rival an avenging angel’s.

“It’s not my fault.” Dean hooted. He eased the Impala out of their parking space and headed up the street.

“Yes, it is,” Sam hotly contested. “Whoever tops brings the condoms and the lube. That’s what you said back in Tampa. That’s the deal we made!”

Dean kicked on the music and cranked up the dial, perfectly content to listen to some AC/DC and grin at Sam’s furious face. “Sorry, dude, can’t hear ya! Music’s too awesome!”

“You’re an asshole, Dean,” Sam hollered back.

Unable to argue the point, Dean shrugged and drove on. In his periphery vision he watched stoically, internally gleeful, as Sam tersely fidgeted trying to find a way to sit that avoided the wet spot that was no doubt forming on the back of his slacks. Nodding along to the music, Dean drummed the beat on the steering wheel, supremely self-satisfied. "So who's up first, Sammy?"

"We should head back to the motel, so I can change."

"No doin', Sammy." Dean rapped the clock on the dashboard with his knuckles. "No time. You'll just have to suck it up, buttercup. And keep your back to the wall."

Sam scowled. Dean beamed, chortling at his own wit.

And on they drove.


End file.
